Ooltewah Whistle Stop offers massive milkshakes and vintage vibes

Staff Photo by Matt Hamilton / Melissa Cain holds a "Chattanooga Shoe Shine Boy Cookies & Cream" milkshake at the Ooltewah Whistle Stop on Thursday, Jan. 14, 2021.
Staff Photo by Matt Hamilton / Melissa Cain holds a "Chattanooga Shoe Shine Boy Cookies & Cream" milkshake at the Ooltewah Whistle Stop on Thursday, Jan. 14, 2021.

Located just a few hundred feet from where the Ooltewah Depot used to sit, the Ooltewah Whistle Stop is close enough to the tracks that diners sitting on the new restaurant's rooftop patio or by the open garage-style doors can feel the wind from passing trains.

The restaurant's vintage theme is reflected in everything from the decor to the flatiron-style building to the specialty milkshakes named after songs from the 1920s-1950s.

"We really wanted to open something themed to a certain era," said Melissa Cain, who opened the restaurant with her husband Josh in early January.

She said the goal was to make the Ooltewah Whistle Stop a place where families, kids and millennials, as well as older adults who remember waiting at the Ooltewah Depot to take the train to Chattanooga, would all feel comfortable.

The Ooltewah residents also felt their town was lacking the sort of unique eatery they search for while traveling in other places, so they set out to change that.

They built the restaurant from the ground up - the couple also own Cain Development, which builds custom homes in the Jasper Highlands community on Jasper Mountain - in the style of the 1920s, inside and out. Along with using the flatiron building shape that was popular in the era, the interior design features custom 1920s-style tile work and vintage pieces such as barstools and light fixtures, and local pictures from the 1920s-50s line the staircases.

The cafe's specialties are comfort foods such as soups, salads and sandwiches. The most popular items include the James County Special, a turkey sandwich with mashed potatoes, dressing and cranberry sauce that was named after the now-defunct James County, Tennessee, of which Ooltewah was the county seat.

"It's like you're favorite holiday meal on a sandwich," Cain said.

The Whistle Stop's true show-stoppers are its milkshakes, which are massive creations that could pass as works of art.

The best-seller is the Chattanooga Shoe Shine Boy Cookies & Cream, featuring cookies and cream ice cream topped with Oreo crumbles, cookies and cream candy bars, zebra cake, devil cake, whipped cream and chocolate drizzle.

Any milkshake can be made "boozy" with the liquor of one's choice.

The Whistle Stop also serves local and regional craft beer, wine, and signature cocktails such as the Tan Shoes with Pink Shoe Laces, a glittery pink concoction made of whipped cream vodka, elderflower liqueur, cranberry juice and glitter cotton candy.

Those celebrating birthdays typically spring for the The Whole Caboose, composed of 16 scoops of ice cream and two each of the following: cookies, brownies, lollipops, doughnuts, waffle cones and sparklers.

Ooltewah Whistle Stop also has vintage video games, such as Pac Man, on the second floor, and the rooftop patio boasts a fire pit, a giant Connect 4 game and even a miniature putting green (Melissa Cain's father is professional golfer Gibby Gilbert II, after all).

Along with local references in the names of menu items, the Whistle Stop also uses as many local products as possible, such as Tasty Donuts and Little Debbie snack cakes on its milkshakes, The Chef and His Wife's pimiento cheese and Chattanooga Brewing Co. beers.

The restaurant seats 130, including the rooftop patio, but the restaurant is not seating at full capacity due to the pandemic.

Hours are Tuesday through Sunday from 11 a.m. to 2 p.m. and 2-5 p.m. To prevent long waits in the cold, most seating is currently by reservation only, though walk-ins are now accepted Tuesdays and Thursdays from 11 a.m. to 2 p.m.

Ooltewah Whistle Stop is at 5503 Main St. in Ooltewah and can be reached at 423-280-1500. Reservations can be made online at ooltewahwhistlestop.com/reservations.

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